Triethylamine → HCID 68508212, compound

HRID 1715425Notes

Reaction equation

HRID 1715425 reaction equation
[C:1]([O:5][C:6](=[O:21])[N:7]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([CH:19]=O)[CH:13]=1)[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH:29]1([NH2:32])[CH2:31][CH2:30]1.[BH4-].[Na+].C([O-])(O)=O.[Na+]>CO>[C:1]([O:5][C:6](=[O:21])[N:7]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([CH2:19][NH:32][CH:29]2[CH2:31][CH2:30]2)[CH:13]=1)[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86622961HCID 86622961, compound

Product 1

HCID 68508212HCID 68508212, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of [2-(4-chloro-3-formyl-phenyl)-ethyl]-ethyl-carbamic acid tert-butyl ester (80.1 mg, 0.257 mmol), Et3N (0.054 mL, 0.386 mmol) and cyclopropylamine (0.027 mL, 0.386 mmol) in MeOH (0.86 mL) was heated to reflux for 4 h. The mixture was allowed to cool to rt, and NaBH4 (24.2 mg, 0.642 mmol) was added in portions. The mixture was stirred for 1 h, and aq. sat. NaHCO3 was added. The mixture was extracted with EtOAc several times, and the combined org. extracts were washed with brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (CH2Cl2/MeOH 95:5) yielded the title compound (40 mg, 44%). LC-MS: tR=0.81 min; ES+: 353.22.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. extractionThe mixture was extracted with EtOAc several times
  4. washextracts were washed with brine
  5. dry with materiallayer was dried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure
  8. customPurification of the residue by FC (CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-617e27462b134b47bf687333d20ce9f5
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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